US10520815B2 - Pattern-forming method - Google Patents

Pattern-forming method Download PDF

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US10520815B2
US10520815B2 US15/460,503 US201715460503A US10520815B2 US 10520815 B2 US10520815 B2 US 10520815B2 US 201715460503 A US201715460503 A US 201715460503A US 10520815 B2 US10520815 B2 US 10520815B2
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group
pattern
forming method
metal
metal compound
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US20170184960A1 (en
US20180017864A9 (en
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Takehiko Naruoka
Tomohisa Fujisawa
Motohiro SHIRATANI
Hisashi Nakagawa
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JSR Corp
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JSR Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
    • G03F7/2006—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light using coherent light; using polarised light
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
    • G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
    • G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
    • H01L21/0274—Photolithographic processes

Definitions

  • the present invention relates to a pattern-forming method.
  • Radiation-sensitive compositions used for microfabrication by lithography generate acids in regions by irradiation with: electromagnetic waves such as far ultraviolet rays, e.g., an ArF excimer laser beam and a KrF excimer laser beam; charged particle rays such as an electron beam; and the like, making a difference in a rate of dissolution in a developer solution between the light-exposed regions and light-unexposed regions, through a chemical reaction in which the acid acts as a catalyst, whereby a resist pattern is formed on a substrate.
  • electromagnetic waves such as far ultraviolet rays, e.g., an ArF excimer laser beam and a KrF excimer laser beam
  • charged particle rays such as an electron beam
  • a pattern-forming method includes applying a radiation-sensitive composition on a substrate to provide a film on the substrate. The film is exposed. The film exposed is developed.
  • the radiation-sensitive composition includes a metal-containing component that is a metal compound having a hydrolyzable group, a hydrolysis product of the metal compound having a hydrolyzable group, a hydrolytic condensation product of the metal compound having a hydrolyzable group, or a combination thereof.
  • a content of a transition metal atom in the metal-containing component with respect to total metal atoms in the metal-containing component is no less than 50 atomic %.
  • FIG. 1 shows a schematic plan view illustrating a line-pattern when seen from above.
  • FIG. 2 shows a schematic cross sectional view illustrating a line-pattern configuration.
  • a pattern-forming method comprises: providing a film from a radiation-sensitive composition (hereinafter, may be also referred to as “film-providing step”); exposing the film (hereinafter, may be also referred to as “exposing step”); and developing the film exposed (hereinafter, may be also referred to as “developing step”), wherein: the radiation-sensitive composition comprises a metal-containing component (hereinafter, may be also referred to as “(A) metal-containing compound” or “metal-containing compound (A)”) that is a metal compound having a hydrolyzable group, a hydrolysis product of the metal compound having a hydrolyzable group, a hydrolytic condensation product of the metal compound having a hydrolyzable group, or a combination thereof; and a content of a transition metal atom with respect to total metal atoms in the metal-containing compound (A) is no less than 50 atomic %.
  • the pattern-forming method of the embodiment of the present invention enables a pattern superior in nanoedge roughness property to be formed with high sensitivity, by using a radiation-sensitive composition superior in storage stability. Therefore, the pattern-forming method can be suitably used for a processing process of semiconductor devices, and the like, in which further progress of miniaturization is expected in the future.
  • embodiments of the present invention will be described in detail. It is to be noted that the present invention is not limited to the following embodiments.
  • the pattern-forming method comprises the film-providing step, the exposing step, and the developing step, and permits the film to be formed from the radiation-sensitive composition comprising the metal-containing compound (A).
  • the film-providing step the exposing step, and the developing step, and permits the film to be formed from the radiation-sensitive composition comprising the metal-containing compound (A).
  • each step is explained.
  • a film is provided by using the radiation-sensitive composition (described later).
  • the film may be provided by, for example, applying the radiation-sensitive composition on a substrate.
  • An application procedure is not particularly limited, and an appropriate application procedure such as spin-coating, cast coating, roller coating, etc. may be employed.
  • the substrate include a silicon wafer, a wafer coated with aluminum, and the like.
  • the composition is applied such that a resulting film has a predetermined thickness, and prebaking (PB) is carried out as needed to evaporate a solvent in the coating film.
  • PB prebaking
  • the lower limit of an average thickness of the coating film is preferably 10 nm.
  • the upper limit of the average thickness of the coating film is preferably 500 nm.
  • the lower limit of the temperature for the PB is generally 60° C., and preferably 80° C.
  • the upper limit of the temperature for the PB is generally 140° C., and preferably 120° C.
  • the lower limit of a time period for the PB is generally 5 sec, and preferably 10 sec.
  • the upper limit of the time period for the PB is generally 600 sec, and preferably 300 sec.
  • an organic or inorganic antireflective film may also be formed beforehand on a substrate to be used, in order to maximize potential of the radiation-sensitive composition.
  • a protective film may be provided on the coating film.
  • a protective film for liquid immersion may also be provided on the film.
  • the film formed in the film-providing step is exposed.
  • the exposure is carried out by irradiating with a radioactive ray through a mask having a predetermined pattern, and through a liquid immersion medium such as water as needed.
  • the radioactive ray is appropriately selected from: electromagnetic waves such as visible light rays, ultraviolet rays, far ultraviolet rays, extreme ultraviolet rays (EUV, wavelength: 13.5 nm), X-rays and ⁇ radiations; charged particle rays such as electron beams and ⁇ -rays; and the like.
  • electromagnetic waves such as visible light rays, ultraviolet rays, far ultraviolet rays, extreme ultraviolet rays (EUV, wavelength: 13.5 nm), X-rays and ⁇ radiations
  • charged particle rays such as electron beams and ⁇ -rays
  • EUV and electron beams are more preferred.
  • post exposure baking may be carried out.
  • the lower limit of a temperature for the PEB is generally 50° C., and preferably 80° C.
  • the upper limit of the temperature for the PEB is generally 180° C., and preferably 130° C.
  • the lower limit of a time period for the PEB is generally 5 sec, and preferably 10 sec.
  • the upper limit of the time period for the PEB is generally 600 sec, and preferably 300 sec.
  • a developer solution to be used in the development is preferably an alkaline developer solution. A negative tone pattern is thereby formed.
  • alkaline developer solution examples include: alkaline aqueous solutions prepared by dissolving at least one of alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, ethyldimethyl amine, triethanolamine, tetramethylammonium hydroxide (TMAH), pyrrole, piperidine, choline, 1,8-diazabicyclo-[5.4.0]-7-undecene and 1,5-diazabicyclo-[4.3.0]-5-nonene; and the like.
  • alkaline aqueous solutions prepared by dissolving at least one of alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia
  • developer solutions may be used either alone of one type, or in combination of two or more types thereof.
  • the development is generally followed by washing with water and the like and drying.
  • the radiation-sensitive composition contains the metal-containing compound (A).
  • the radiation-sensitive composition is not particularly limited as long as the metal-containing compound (A) is contained therein, and may also contain other components such as a solvent (B), a surfactant, and the like. Hereinafter, each component will be described.
  • the metal-containing compound (A) (metal-containing component) is: a metal compound (I) having a hydrolyzable group; a hydrolysis product of the metal compound (I) having a hydrolyzable group; a hydrolytic condensation product of the metal compound (I) having a hydrolyzable group; or a combination thereof.
  • a content of a transition metal atom with respect to total metal atoms in the metal-containing compound (A) is no less than 50 atomic %.
  • the hydrolyzable group is exemplified by a halogen atom, an alkoxy group, a carboxylate group, and the like.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and the like.
  • carboxylate group examples include: a formate group; alkylcarbonyloxy groups having no greater than 5 carbon atoms such as an acetate group, a propionate group and a butyrate group; a stearate group, a benzoate group, an oxalate group, a (meth)acrylate group, and the like.
  • a halogen atom, an alkoxy group and a carboxylate group are preferred, and a chlorine atom, an isopropoxy group, a butoxy group, a formate group, an alkylcarbonyloxy group having no greater than 5 carbon atoms, and a (meth)acrylate group are more preferred.
  • a transition metal atom is exemplified by atoms of metal elements from groups 3, 4, 5, 6, 7, 8, 9, 10, and 11. Of these, atoms of metal elements from the groups 4, 5, 6, 8, 9 and 10 are preferred, and atoms of zirconium, titanium, hafnium, tungsten, ruthenium and cobalt are preferred, and atoms of zirconium and titanium are more preferred.
  • the metal compound (I) may be used either alone of one type, or in combination of two or more types thereof.
  • the hydrolytic condensation product of the metal compound (I) may be any of: a hydrolytic condensation product of only a transition metal compound having a hydrolyzable group; a hydrolytic condensation product of a transition metal compound having a hydrolyzable group, and a compound having a hydrolyzable group and comprising a metal atom other than a transition metal atom; and a hydrolytic condensation product of only a compound having a hydrolyzable group and comprising a metal atom other than the transition metal atom.
  • the metal element other than the transition metal is exemplified by aluminum, silicon, and the like.
  • the lower limit of a content of the transition metal atom with respect to total metal atoms in the metal-containing compound (A) is preferably 60 atomic %, more preferably 70 atomic %, further more preferably 80 atomic %, and particularly preferably 90 atomic %.
  • the upper limit of the content is preferably 100 atomic %, and more preferably 98 atomic %.
  • the upper limit of a content of the metal atom other than the transition metal atom with respect to total metal atoms in the metal-containing compound (A) is preferably 50 atomic %, more preferably 30 atomic %, and further more preferably 10 atomic %.
  • the metal compound (I) having a hydrolyzable group in which the metal atom is the transition metal atom is exemplified by compounds represented by the following formula (1), and the like.
  • M represents the transition metal atom
  • L represents a ligand, and a is 1 or 2, wherein in a case where a is 2, a plurality of Ls are identical or different
  • X represents a hydrolyzable group selected from a halogen atom, an alkoxy group, and a carboxylate group, and b is an integer of 2 to 6, wherein in a case where b is no less than 2, a plurality of Xs are identical or different, and wherein L represents a ligand that does not fall under the definition of X.
  • the transition metal atom represented by M is exemplified by atoms of metal elements from groups 3, 4, 5, 6, 7, 8, 9, 10, and 11. Of these, atoms of metal elements from the groups 4, 5, 6, 8, 9 and 10 are preferred, and atoms of zirconium, titanium, hafnium, tungsten, ruthenium and cobalt are preferred, and zirconium and titanium are more preferred.
  • the ligand represented by L is exemplified by a monodentate ligand and a polydentate ligand.
  • Examples of the monodentate ligand include a hydroxo ligand, carboxy ligands, amido ligands, and the like.
  • amido ligand examples include an unsubstituted amido ligand (NH 2 ), a methylamido ligand (NHMe), a dimethylamido ligand (NMe 2 ), a diethylamido ligand (NEt 2 ), a dipropylamido ligand (NPr 2 ), and the like.
  • Exemplary polydentate ligand includes a hydroxy acid ester, a ⁇ -diketone, a ⁇ -ketoester, a ⁇ -dicarboxylic acid ester, a hydrocarbon having a ⁇ bond, a phosphine, a carboxylic acid, ammonia, and the like.
  • hydroxy acid ester examples include glycolic acid esters, lactic acid esters, 2-hydroxycyclohexane-1-carboxylic acid esters, salicylic acid esters, and the like.
  • ⁇ -diketone examples include acetylacetone, methylacetylacetone, ethylacetylacetone, 3-methyl-2,4-pentanedione, and the like.
  • ⁇ -keto ester examples include acetoacetic acid esters, ⁇ -alkyl-substituted acetoacetic acid esters, ⁇ -ketopentanoic acid esters, benzoylacetic acid esters, 1,3-acetonedicarboxylic acid esters, and the like.
  • ⁇ -dicarboxylic acid ester examples include malonic acid diesters, ⁇ -alkyl-substituted malonic acid diesters, ⁇ -cycloalkyl-substituted malonic acid diesters, ⁇ -aryl-substituted malonic acid diesters, and the like.
  • hydrocarbon having a it bond examples include:
  • chain olefins such as ethylene and propylene
  • cyclic olefins such as cyclopentene, cyclohexene and norbornene
  • chain dienes such as butadiene and isoprene
  • cyclic dienes such as cyclopcntadiene, methylcyclopentadiene, pentamethylcyclopentadiene, cyclohexadiene and norbornadiene;
  • aromatic hydrocarbons such as benzene, toluene, xylene, hexamethylbenzene, naphthalene and indene; and the like.
  • Examples of the phosphine includes 1,1-bis(diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, and the like.
  • the carboxylic acid is preferably a monocarboxylic acid having no less than 6 carbon atoms, examples of which include caprylic acid, caprylic acid, capric acid, stearic acid, benzoic acid, and the like.
  • a monocarboxylic acid having no less than 6 carbon atoms, a hydroxy acid ester, a ⁇ -diketone, a ⁇ -ketoester, a ⁇ -dicarboxylic acid ester, a hydrocarbon having a ⁇ bond, a phosphine, and a combination thereof are preferred; a lactic acid ester, an acetylacetone, an acetoacetic acid ester, a malonic acid diester, a cyclic diene, a phosphine, a carboxylate anion, and a combination thereof are more preferred; and an acetylacetone is are further more preferred.
  • halogen atom which may be represented by X include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • alkoxy group which may be represented by X include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and the like.
  • carboxylate group which may be represented by X
  • a formate group and an alkylcarbonyloxy group having no greater than 5 carbon atoms are preferred.
  • alkylcarbonyloxy group having no greater than 5 carbon atoms include an acetate group, a propionate group, a butyrate group, a valerate group, and the like.
  • X represents preferably a halogen atom, an alkoxy group or a carboxylate group, and more preferably a chlorine atom, an isopropoxy group, a butoxy group, a formate group, an alkylcarbonyloxy group having no greater than 5 carbon atoms, or a (meth)acrylate group.
  • b is preferably an integer of 2 to 4, more preferably 2 or 3, and still more preferably 2.
  • the compound represented by the formula (1) preferably has 2 to 4 Xs.
  • Examples of the metal compound (I) having a hydrolyzable group in which the metal atom is the transition metal atom include zirconium di-n-butoxide bis(2,4-pentanedionate), titanium tri-n-butoxide stearate, bis(cyclopentadienyl)hafnium dichloride, bis(2,4-pentanedionato)dimethacryloyloxyhafnium, bis(cyclopentadienyl)tungsten dichloride, diacetato[(S)-( ⁇ )-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium, dichloro[ethylenebis[diphenylphosphine]]cobalt, a titanium butoxide oligomer, aminopropyltrimethoxytitanium, aminopropyltriethoxyzirconium, 2-(3,4-epoxycyclohexyl)ethyltrimeth
  • the content of the metal-containing compound (A) in the radiation-sensitive composition with respect to the total solid content in the radiation-sensitive composition is preferably no less than 70% by mass, more preferably no less than 80% by mass, and further more preferably no less than 85% by mass.
  • the radiation-sensitive composition is superior in storage stability and enables a pattern superior in the nanoedge roughness property to be formed with high sensitivity.
  • the reason for achieving the effects described above due to the radiation-sensitive composition comprising the metal-containing compound (A) is inferred as in the following, for example.
  • the hydrolyzable group and/or the ligand in the metal-containing compound (A) would dissociate from the transition metal atom and metal atoms bind to one another, whereby a pattern superior in the nanoedge roughness property is enabled to be formed with high sensitivity, in which light-exposed regions are insoluble in a developer solution such as an alkaline solution.
  • the pattern thus formed is a negative tone pattern.
  • the radiation-sensitive composition attains superior storage stability, since the radiation-sensitive composition does not require a polymer having an acid-labile group and an acid generator, which have been required for conventional chemically amplified radiation-sensitive compositions, and, even if an acid generator is present, the radiation-sensitive composition would not be adversely affected thereby.
  • the radiation-sensitive composition typically contains the solvent (B).
  • the solvent (B) is not particularly limited as long as it is a solvent capable of dissolving or dispersing at least the metal-containing compound (A), as well as other component(s) comprised as needed.
  • the solvent (B) may be used either alone of one type, or in combination of two or more types thereof.
  • the solvent (B) is exemplified by alcohol solvents, ether solvents, ketone solvents, amide solvents, ester solvents, hydrocarbon solvents, and the like.
  • alcohol solvents examples include:
  • aliphatic monohydric alcohol solvents having 1 to 18 carbon atoms such as 4-methyl-2-pentanol and n-hexanol;
  • alicyclic monohydric alcohol solvents having 3 to 18 carbon atoms such as cyclohexanol
  • polyhydric alcohol solvents having 2 to 18 carbon atoms such as 1,2-propylene glycol
  • polyhydric alcohol partially etherated solvents having 3 to 19 carbon atoms such as propylene glycol monomethyl ether; and the like.
  • ether solvents examples include:
  • dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether and diheptyl ether;
  • cyclic ether solvents such as tetrahydrofuran and tetrahydropyran
  • aromatic ring-containing ether solvents such as diphenyl ether and anisole; and the like.
  • ketone solvents examples include:
  • chain ketone solvents such as acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl n-butyl ketone, diethyl ketone, methyl iso-butyl ketone, 2-heptanone, ethyl n-butyl ketone, methyl n-hexyl ketone, di-iso-butyl ketone and trimethylnonanone;
  • cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone; 2,4-pentanedione, acetonylacetone and acetophenone; and the like.
  • amide solvents examples include:
  • cyclic amide solvents such as N,N′-dimethylimidazolidinone and N-methylpyrrolidone
  • chain amide solvents such as N-methylformamide, N,N-dimethylformamide, N,N-diethylformamide, acetamide, N-methylacetamide, N,N-dimethylacetamide and N-methylpropionamide; and the like.
  • ester solvents examples include:
  • monocarboxylic acid ester solvents such as n-butyl acetate and ethyl lactate;
  • polyhydric alcohol carboxylate solvents such as propylene glycol acetate
  • polyhydric alcohol partially etherated carboxylate solvents such as propylene glycol monomethyl ether acetate
  • polyhydric carboxylic acid diester solvents such as diethyl oxalate
  • carbonate solvents such as dimethyl carbonate and diethyl carbonate; and the like.
  • hydrocarbon solvents examples include:
  • aliphatic hydrocarbon solvents having 5 to 12 carbon atoms such as n-pentane and n-hexane;
  • aromatic hydrocarbon solvents having 6 to 16 carbon atoms such as toluene and xylene; and the like.
  • alcohol solvents are preferred; polyhydric alcohol partially etherated solvents, polyhydric alcohol partially etherated carboxylate solvents and cyclic ketone solvents are more preferred; and propylene glycol monomethyl ether, propylene glycol monoethyl ether acetate and cyclohexanone are particularly preferred.
  • the radiation-sensitive composition may contain other component in addition to the aforementioned components (A) and (B).
  • the other component is exemplified by a surfactant, an acid generator, a silicon compound having a hydrolyzable group, a hydrolysis product thereof, a hydrolytic condensation product thereof, and the like. These other components may be used either alone of one type, or in combination of two or more types thereof.
  • the surfactant is a component that exhibits the effect of improving coating properties, striation and the like.
  • the surfactant include: nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, and polyethylene glycol dilaurate and polyethylene glycol distearate; commercially available products such as KP341 (Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75 and Polyflow No.
  • the lower limit of a content of the surfactant is preferably 0.01 parts by mass, more preferably 0.02 parts by mass, further more preferably 0.05 parts by mass, and particularly preferably 0.08 parts by mass, with respect to 100 parts by mass of the metal-containing compound (A).
  • the upper limit of the content of the surfactant is preferably 1 part by mass, more preferably 0.5 parts by mass, and further more preferably 0.2 parts by mass.
  • the radiation-sensitive composition comprises the acid generator
  • an effect of improving dissolution contrast may be achieved.
  • Known acid generators used in chemically amplified resist materials may be used.
  • the acid generator is exemplified by onium salt compounds, N-sulfonyloxyimide compounds, halogen-containing compounds, diazo ketone compounds, and the like. Of these acid generators, onium salt compounds are preferred.
  • Exemplary onium salt compounds include sulfonium salts, tetrahydrothiophenium salts, iodonium salts, phosphonium salts, diazonium salts, pyridinium salts, and the like.
  • sulfonium salt examples include: triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium perfluoro-n-octanesulfonate, triphenylsulfonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, triphenylsulfonium camphorsulfonate, 4-cyclohexylphenyldiphenylsulfonium trifluoromethanesulfonate, 4-cyclohexylphenyldiphenylsulfonium nonafluoro-n-butanesulfonate, 4-cyclohexylphenyldiphenylsulfonium perfluoro-n-octanesulfonate, 4-cyclohexylpheny
  • tetrahydrothiophenium salt examples include 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium trifluoromethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium perfluoro-n-octanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophenium camphorsulphonate, 1-(4-n-butoxynaphthalen-1-yl)tetrahydrothiophen
  • iodonium salt examples include: diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate, diphenyliodonium camphorsulfonate, bis(4-t-butylphenyl)iodonium trifluoromethanesulfonate, bis(4-t-butylphenyl)iodonium nonafluoro-n-butanesulfonate, bis(4-t-butylphenyl)iodonium perfluoro-n-octanesulfonate, bis(4-t-butylphenyl)iodonium 2-bicyclo
  • N-sulfonyloxyimide compound examples include N-(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(nonafluoro-n-butanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(perfluoro-n-octanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-bicyclo[2.2.1]hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-(3-tetracyclo[4.4.0.1 2,5 .1 7,10 ]dodecanyl)-1,1-difluoroethane
  • onium salts are preferred, sulfonium salts and tetrahydrothiophenium salts are more preferred, triphenylsulfonium salts and 1-(4-n-butoxynaphthalene-1-yl)tetrahydrothiophenium salts are further more preferred, and triphenylsulfonium 2-(1-adamantyl)-1,1-difluoroethanesulfonate, triphenylsulfonium 2-(adamantane-1-yl carbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate, 1-(4-n-butoxynaphthalene-1-yl)tetrahydrothiophenium hexafluoropropylene sulfonimide and triphenylsulfonium nonafluoro-n-butanesulfonate are particularly preferred.
  • the lower limit of a content of the acid generator is preferably 0.05 parts by mass, more preferably 0.1 parts by mass, further more preferably 1 part by mass, and particularly preferably 5 parts by mass, with respect to 100 parts by mass of the metal-containing compound (A).
  • the upper limit of the content of the acid generator is preferably 30 parts by mass, and more preferably 25 parts by mass.
  • the radiation-sensitive composition may be prepared, for example, by mixing the metal-containing compound (A) and the solvent (B), as well as other components such as the surfactant and the acid generator as needed, at a certain ratio.
  • the radiation-sensitive composition may be prepared in normal use by further adding a solvent to adjust the concentration thereof, and thereafter filtering the solution through a filter having a pore size of, for example, about 0.2 ⁇ m.
  • the lower limit of the solid content concentration of the radiation-sensitive composition is preferably 0.1% by mass, more preferably 0.5% by mass, further more preferably 1% by mass, and particularly preferably 1.5% by mass.
  • the upper limit of the solid content concentration is preferably 50% by mass, more preferably 30% by mass, further more preferably 20% by mass, and particularly preferably 10% by mass.
  • the metal-containing compound (A), the solvent (B), the acid generator, and the surfactant used for preparing the radiation-sensitive composition are shown below.
  • A-1 zirconium(IV) di-n-butoxide bis(2,4-pentanedionate) (60% by mass solution in butanol)
  • A-2 titanium(IV) tri-n-butoxide stearate (90% by mass solution in butanol)
  • A-3 bis(cyclopentadienyl)hafnium(IV) dichloride
  • A-4 bis(2,4-pentanedionato)dimethacryloyloxyhafnium
  • A-6 diacetato[(S)-( ⁇ )-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium(II) ((S)—Ru(OAc) 2 (BINAP))
  • A-8 titanium(IV) butoxide oligomeric decamer ([TiO(OBu) 2 ] 10 )
  • A-11 tri(isopropoxy)aluminum
  • PGEE propylene glycol monoethyl ether
  • PGMEA propylene glycol monomethyl ether acetate
  • Zirconium(IV) di-n-butoxide bis(2,4-pentanedionate) (60% by mass solution in butanol) (A-1) was diluted with a solvent (propylene glycol monoethyl ether) to give a mixed solution having a concentration of the metal-containing compound (A) of 5% by mass.
  • the resulting solution was filtered through a membrane filter having a pore size of 0.20 ⁇ m, to thereby prepare a radiation-sensitive composition (R-1).
  • Radiation-sensitive compositions (R-2) to (R-12) were prepared by a similar operation to that of Preparation Example 1 except that the type and the content of each component used were as shown in Table 1. In relation to other components, the symbol “-” indicates that the corresponding component was not added.
  • Zirconium(IV) di-n-butoxide bis(2,4-pentanedionate) (60% by mass solution in butanol) (A-1) was mixed with tri(isopropoxy)aluminum (A-11) at such a quantitative ratio that a molar ratio of the compounds (A-1)/(A-11) was 60/40, and the mixture was diluted with a solvent (propylene glycol monoethyl ether), to give a mixed solution having a concentration of the metal-containing compound (A) of 5% by mass.
  • the resulting solution was filtered through a membrane filter having a pore size of 0.20 ⁇ m, to thereby prepare a radiation-sensitive composition (R-11).
  • Zirconium(IV) di-n-butoxide bis(2,4-pentanedionate) (60% by mass solution in butanol) (A-1) was mixed with tri(isopropoxy)aluminum (A-11) at such a quantitative ratio that a molar ratio of the compounds (A-1)/(A-11) was 40/60, and the mixture was diluted with a solvent (propylene glycol monoethyl ether) to give a mixed solution having a concentration of the metal-containing compound (A) of 5% by mass.
  • the resulting solution was filtered through a membrane filter having a pore size of 0.20 ⁇ m, to thereby prepare a radiation-sensitive composition (R-12).
  • the radiation-sensitive composition shown in the above Table 1 was spin-coated onto a silicon wafer in “CLEAN TRACK ACT-8” available from Tokyo Electron Limited, and subjected to PB at 80° C. for 60 sec to form a film having an average thickness of 50 nm. Subsequently, the film was irradiated with an electron beam using a simplified electron beam writer (“HL800D” available from Hitachi, Ltd., power: 50 keV, current density: 5.0 ampere/cm 2 ) to permit patterning. Following the irradiation with the electron beam, a development was carried out according to a puddle procedure at 23° C. for 1 min using a 2.38% by mass aqueous tetramethylammonium hydroxide solution in the CLEAN TRACK ACT-8. Thereafter, the substrate was washed with pure water and then dried, whereby a pattern was formed.
  • a simplified electron beam writer (“HL800D” available from Hitachi, Ltd., power: 50 keV, current
  • optical exposure dose An exposure dose at which a line and space pattern (1L 1S) configured with a line part having a line width of 150 nm and a space part formed by neighboring line parts with an interval of 150 nm was formed to give a line width of 1:1 was defined as “optimal exposure dose”, and the “optimal exposure dose” was defined as “sensitivity” ( ⁇ C/cm 2 ).
  • the line patterns of the line and space pattern (1L 1S) were observed using a scanning electron microscope for semiconductor (high-resolution FEB critical dimension measurement device “S-9220” available from Hitachi, Ltd.). Arbitrary fifty points on the pattern were observed, and with respect to the observed shape, a difference “ ⁇ CD” between an intended line width of 150 nm and a line width in an area in which irregularities generated along the side lateral surface 2a of the line part 2 of the pattern formed on the silicon wafer 1 was most significant was measured as shown in FIGS. 1 and 2 , by using CD-SEM (“S-9220” available from Hitachi High-Technologies Corporation). The ACD value was defined as “nanoedge roughness” (nm).
  • the nanoedge roughness property was determined to be: “AA (extremely favorable)” in the case of being no greater than 15.0 nm; “A (favorable)” in the case of being greater than 15.0 nm and no greater than 16.5 nm; and “B (unfavorable)” in the case of being greater than 16.5 nm.
  • the evaluation “C” is indicated in the table. It is to be noted that the irregularities shown in FIGS. 1 and 2 are exaggerated.
  • Patterning was evaluated in a similar manner to the aforementioned procedure, immediately after the preparation of the radiation-sensitive composition and after storage at room temperature for two weeks.
  • the storage stability was determined to be: “AA” in the case of a change in sensitivity being no greater than 5%; “A” in the case of the change in sensitivity being no greater than 10%; and “B” in a case of a failure to form a pattern.
  • the pattern-forming method of the embodiment of the present invention enables a pattern superior in nanoedge roughness property to be formed with high sensitivity, by using a radiation-sensitive composition superior in storage stability. Therefore, the pattern-forming method can be suitably used for a processing process of semiconductor devices, and the like, in which further progress of miniaturization is expected in the future.

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US9310684B2 (en) 2013-08-22 2016-04-12 Inpria Corporation Organometallic solution based high resolution patterning compositions
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EP4089482A1 (fr) 2015-10-13 2022-11-16 Inpria Corporation Compositions organostanniques d'oxyde/hydroxyde pour formation de motifs, précurseurs et formation de motifs
JP2018017780A (ja) * 2016-07-25 2018-02-01 Jsr株式会社 感放射線性組成物及びパターン形成方法
JPWO2018168221A1 (ja) * 2017-03-13 2020-01-16 Jsr株式会社 感放射線性組成物及びパターン形成方法
WO2019021975A1 (fr) * 2017-07-24 2019-01-31 Jsr株式会社 Composition de formation de film contenant du métal pour usage en lithographie extrême ultraviolet ou en lithographie par faisceau d'électrons, film contenant du métal pour usage en lithographie extrême ultraviolet ou en lithographie par faisceau d'électrons, et procédé de formation de motifs
JP7264771B2 (ja) * 2019-08-30 2023-04-25 信越化学工業株式会社 レジスト材料及びパターン形成方法

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